


Sexting 101 With Dean And Cas

by thelonelywriter



Category: Supernatural
Genre: Alternate Universe - High School, Bottom Dean, Dick Pics, Dirty Talk, Fluff and Smut, M/M, Masturbation, Mutual Masturbation, Phone Sex, Plot What Plot/Porn Without Plot, Sexting, Some Humor, Teenage Castiel/Teenage Dean Winchester, Top Castiel
Language: English
Status: Completed
Published: 2016-11-21
Updated: 2016-11-21
Packaged: 2018-09-01 07:20:31
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,948
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8614825
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: Cas has been away for a week on vacation with his family, so Dean comes up with a bright idea of what they can do instead of sitting around missing each other.





	

**Author's Note:**

> Ughhh, it's like three in the morning I should be in bed. I'm posting this though because I know if I don't post it tonight I'll be upset so anyways, yeah, I came up with this idea and I mentioned it on Tumblr and you guys really liked it so I went ahead and wrote it. Dean's texts are in bold and Cas' texts are in italics. Please appreciate them bc it took me like half of my life to put in the little things to signify that they're bolded or whatever. (It's tagged as underage but I would pin them as about 18 anyways. If you want them younger feel free to imagine it that way, whatever toots ya horn my friend.)

It had been about a week since Cas had seen Dean and he was totally and utterly done with the fact of it.

 

Cas’ family had rented a cabin somewhere completely obsolete in hopes of some time together for the winter season, that space between Thanksgiving and Christmas. Cas, being a normal teenage boy, had been quite begrudging about the trip, especially since his boyfriend, Dean, would be miles away from him for the duration of the trip.

 

They had kissed goodbye and Cas had promised Dean it wasn’t the end of the world, even though Cas wasn’t so sure about that. They had both promised to keep in touch, and for the most part they have been, Dean texting Cas or Cas texting Dean sometimes during the day, sometimes at night to say goodnight. So, it’s no surprise when Cas has just finished dinner and is heading off to his room to try and relax alone when his phone buzzes in his pocket. It’s a miracle that he even gets reception, but he’s definitely not going to question it.

 

He pulls his phone out of his pocket, reading the notification from Dean as he closes his door. ‘ **hey** ’ it says simply, and Cas smiles a little, even though it’s nothing too earth shattering.

 

‘ _Hey_ ,’ Cas types out in response as he heads towards his bed, crawling atop it and lying back on the pillows.

 

‘ **you doing anything?** ’ is the reply that comes fairly quickly.

 

‘ _Nah, just finished dinner. You?_ ’ Castiel hits the send button, then opens up the Tumblr app, passing some time when his phone dings and a little reply is hovering at the top of Cas’ screen.

 

‘ **just finished helping sammy with his homework. why is their math so difficult? He’s four years younger and they’re like on the quadratic formula or some shit.** ’ Cas reads. Cas snorts a laugh, immediately going to reply when another message pops up. ‘ **system’s rigged man, i swear**.’

 

Cas laughs even harder at that.

 

‘ _You got any conspiracy theories about that yet?_ ’

 

‘ **yeah, just you wait,** ’ Dean replies. Cas smiles fondly.

 

‘ _Other than plotting conspiracy theories on the school system, what else are you doing?_ ’

 

‘ **Missing you.** ’

 

Cas’ heart does a little flutter as he smiles widely.

 

‘ _I miss you too,_ ’ Cas replies, wishing that this vacation would be over so that he could just go home and see Dean.

 

‘ **how much?** ’

 

‘ _As much as the stars love the sky._ ’

 

‘ **you’re too cheesy for me.** ’

 

‘ _You were the one who asked me out._ ’

 

‘ **yeah, because your cute.** ’

 

‘ _*You’re._ ’

 

‘ **i take that back.** ’

 

Cas laughs a little more at that response, pausing before typing something else out.

 

‘ _How much do you miss me?_ ’

 

‘ **Like the moon misses the sun.** ’

 

A pause.

 

‘ **or something like that.** ’

 

Cas smiles.

 

‘ _You should be a poet,_ ’ Cas teases. Where Dean is, lying on his bed in his own house, he rolls his eyes.

 

‘ **maybe I will, just to spite you,** ’ Dean texts back. Where Cas is lying on his bed he raises an eyebrow.

 

‘ _What kinds of poems will you write?_ ’

 

‘ **Poems about your eyes,** ’ Dean texts back, smiling softly. Cas blushes.

 

‘ _Oh?_ ’

 

‘ **yeah. I can see it now,** ’ Dean goes on. 

 

‘ **His eyes are as blue as the ocean,** ’ Dean writes. 

 

‘ **Unfathomable and mysterious.** ’ Dean frowns. 

 

‘ **Fathomable? I don’t know. They’re just really pretty.** ’

 

Cas feels his heart flutter and he smiles.

 

‘ **I’ll get the kinks out when I’m in the publishing process,** ’ Dean teases.

 

‘ _Will you sign my copy once it’s published?_ ’

 

‘ **I’ll sign whatever you want.** ’

 

‘ **;)** ’

 

Cas groans.

 

‘ _Dean, you’re terrible._ ’

 

‘ **what? it was a perfect segway!** ’ Dean argues.

 

‘ _Into what exactly?_ ’ Castiel inquires, his interest piqued just the slightest. There’s a longer pause than usual between the last text and Dean’s next one.

 

‘ **well, I was thinking. i have this idea.** ’

 

Cas raises his eyebrows again and is quick to type out a reply.

 

‘ _Pray do tell._ ’

 

‘ **well, I haven’t seen you in like awhile.** ’

 

‘ _Yeah?_ ’

 

‘ **and I haven’t kissed you in awhile.** ’

 

Cas has a feeling where this is going but he continues on.

 

‘ _And?_ ’

 

‘ **i haven’t touched you or anything.** ’

 

‘ **in a while.** ’

 

‘ **and I’d really like to but I can’t so…** ’

 

‘ _So?_ ’

 

‘ **So I thought maybe we could try sexting,** ’ Dean suggests, a little nervous that Cas will totally look his nose up at Dean, thinking that it’s completely weird. Dean’s not really afraid of being turned down, he’d totally understand if Cas just didn’t want to, he’s more afraid of what Cas might think.

 

Lucky for him, at the proposal, something interesting runs through Cas, something like excitement and that feeling he gets when Dean gives him that Dean look that Cas knows means Dean is gonna find a way into his pants later on in the day.

 

‘ _Do you have any experience with this?_ ’ Cas questions since he knows Dean has had a few girlfriends before him. Where Dean is, he blushes.

 

‘ **no.** ’

 

Quickly followed by,

 

‘ **do you?** ’ 

 

Even though Dean is pretty much certain Cas has never sexted before. Sure enough,

 

‘ _No,_ ’ Cas replies. There’s a pase between them before Dean hurriedly types out,

 

‘ **we don’t have to, really, i don’t mind if you don’t want to do it.** ’

 

‘ **it’s just a random idea.** ’

 

Cas takes a deep breath.

 

‘ _We can try it._ ’

 

Dean lights up on the other end.

 

‘ **really?** ’

 

‘ **you’re sure?** ’ quickly follows it. Cas can’t help but smile. He can practically hear the excitement in Dean’s voice, even though they’re only texting.

 

‘ _Yeah_ ,’ Cas replies simply. Cas watches as the little bubble letting him know Dean is typing pop up, then disappear. There’s a pause after that where Cas figures Dean is trying to come up with something to say.

 

‘ _Did you have a plan on how to start?_ ’ Cas questions, and Dean feels a little embarrassed.

 

‘ **not, uh, really? I honestly wasn’t so sure you’d even want to do it,** ’ Dean tells Cas. Cas chews on his lip for a second.

 

‘ _You want me to start?_ ’

 

‘ **do you want to start?** ’

 

‘ _Well someone has to start._ ’

 

Dean rolls his eyes.

 

‘ **yeah, alright, you start,** ’ Dean relents. Cas smirks a little.

 

‘ _Okay. Where are you?_ ’ 

 

‘ **my bedroom,** ’ Dean replies.

 

‘ _On your bed?_ ’

 

‘ **yeah.** ’

 

‘ _Lying down?_ ’

 

‘ **yeah.** ’ 

 

Another pause happens between them wherein Cas waits to see if Dean will reciprocate, but no typing bubble shows up, even though Cas can see that Dean’s read it.

 

‘ _Feel free to jump in at any time,_ ’ Cas teases.

 

‘ **you’re doing fine though,** ’ Dean insists.

 

‘ _Yeah but it would be fun if you told me a little more._ ’

 

‘ **like what?** ’

 

‘ _You know what,_ ’ Castiel replies, already blushing a little. Dean smirks on the other end.

 

‘ _Tell me more about yourself._ ’

 

‘ **I’m Dean Winchester, I’m an aquarius, I like long walks on the beach, sunsets…** ’

 

‘ _You’re obnoxious._ ’

 

‘ **I’m head over heels for this nerdy guy who wants me to sext him.** ’

 

‘ _You were the one who proposed the idea!_ ’

 

‘ **hah, yeah, i know, i know,** ’ Dean replies, chuckling a little bit as Cas, on his end, shakes his head.

 

**‘okay, alright, serious time.** ’

 

‘ **say something sexy.** ’

 

‘ **light the mood, Cas,** ’ Dean goes on. Cas rolls his eyes again.

 

‘ _I’m not gonna ask you what you’re thinking about because you’re probably thinking about something… I have no idea but probably totally off topic._ ’

 

‘ _Instead, what would you /like/ to be thinking about?_ ’

 

Dean’s heart does a little jump. He knows pretty much exactly what he wants to be thinking about but to tell Cas so explicitly seems… a little difficult.

 

‘ **kissing you.** ’

 

‘ _Where?_ ’

 

‘ **christ, cas, everywhere, i don’t know man.** ’

 

Cas smiles at that one.

 

‘ _Everywhere?_ ’

 

‘ **yeah.** ’

 

‘ _My lips?_ ’

 

‘ **yeah.** ’

 

‘ _My chest?_ ’

 

‘ **yes.** ’

 

‘ _Stomach?_ ’

 

Dean licks his lips. He has an idea of where Cas is going now.

 

‘ **yeah.** ’

 

‘ _And my…?_ ’ 

 

‘ **kiss your dick?** ’

 

Dean immediately regrets sending it and turns red.

 

‘ **that sounded so weird oh my god,** ’ he sends a second later whilst Cas is on his end trying not to laugh out loud.

 

‘ **I would suck you I wouldn’t just.. nevermind, god,** ’ Dean trails off, shaking his head.

 

‘ _What position?_ ’

 

‘ **you against the wall, me on my knees with you. y’know. in my mouth,** ’ Dean goes on, and he has to admit that he’s still red. Cas is blushing too, but not really from embarrassment. 

 

‘ _You’re really good at that._ ’

 

Before Dean can ask for clarification, another text from Cas is coming in (haha).

 

‘ _Sucking cock._ ’

 

‘ _I like you on your knees._ ’

 

Dean takes a long pause because Cas doesn’t usually talk like that and oh my God is it hot when he does. Dean has to remind himself to take a few deep breaths before he goes on.

 

‘ **yeah?** ’

 

‘ _Yeah._ ’

 

‘ _But I like you on your back too._ ’

 

Dean swallows thickly at the words.

 

‘ **you’re surprisingly good at this.** ’

 

‘ _At sexting or fucking you?_ ’

 

Dean has to take a few more deep breaths.

 

‘ **well, uh, kind of both at the moment.** ’

 

Cas smiles triumphantly. Erotic fanfiction has its pay offs.

 

‘ _Are you getting hard?_ ’

 

‘ **kind of difficult not to when you’re telling me you like me on my knees because i’m good at sucking your cock,** ’ Dean jokes back. Cas grins.

 

‘ **are you hard?** ’

 

Cas glances down and shifts around a little. 

 

‘ _Getting there. Not all the way yet,_ ’ Cas tells Dean who frowns.

 

‘ _Maybe you could do some talking too to help that along,_ ’ Cas suggests. Dean rolls his eyes.

 

‘ **cas, i don’t take AP english like you. i don’t like read shakespeare unless I have too.** ’

 

‘ _I don’t either??_ ’

 

‘ **off topic.** ’

 

‘ **i’m just saying, i’m not like a flowery speaker or whatever. i don’t like write love letters. i’m not good at that kind of stuff,** ’ Dean explains.

 

‘ _You don’t have to be good at it. You can be totally shit at it._ ’

 

‘ _Which you’re not._ ’

 

‘ _But just tell me what you’re thinking, what you want, whatever. It doesn’t have to be pretty or flowery. It can be blunt and just… a random statement. I don’t care,_ ’ Castiel encourages. A little bit of Dean’s nerves fall away at the words. He knows Cas won’t judge.

 

‘ **i like when you fuck me on all fours,** ’ Dean blurts out because it’s on his mind and Cas said to say that kind of stuff and it makes him harder just thinking about it so why not share?

 

‘ _Yeah?_ ’ Castiel replies, his own dick twitching happily at the statement. 

 

‘ **especially when you, y’know…** ’

 

‘ _???_ ’

 

‘ **when you touch me. like, when you jerk me off while you’re fucking me,’** Dean goes on, his heart beating faster. Cas’ does the same, and his cock rises up a little more.

 

‘ _I do too,_ ’ Cas agrees.

 

‘ _But I like when you come untouched too._ ’

 

Dean bites back a moan at just the thought. 

 

‘ _And I like it when we don’t use condoms. I like coming inside of you,_ ’ Cas tells Dean. Dean actually does let out a soft moan at the text because he fucking loves when they don’t use condoms and Cas comes inside of him.

 

‘ _I like when you let me finger you after we fuck,_ ’ Cas goes on.

 

‘ **fuck i love when you do that,** ’ Dean replies, noting the fact that his cock is straining against his jeans almost uncomfortably. 

 

‘ **hang on a sec,** ’ Dean says, placing the phone down and undoing the button and zipper of his jeans, hooking his fingers in his jeans and his boxers, awkwardly tugging them down until his cock sprang free. He tossed them aside before sitting up, tugging his shirt over his head, figuring why not go all out when he knew that his door was definitely locked.

 

‘ **okay, continue,** ’ Dean types out.

 

‘ _Why don’t you continue? Tell me what exactly you were just doing._ ’

 

‘ **getting naked,** ’ Dean replies bluntly.

 

‘ **wanna join?** ’

 

Cas smirks a little.

 

‘ _give me a sec._ ’

 

Cas sits up, rolling out of bed so that he can drop down his jeans and his boxers, then get his shirt off. He goes over to the door, double checking that it’s locked before bouncing back onto the bed, this time grinning as he lies on his stomach instead of his back.

 

‘ _Alright._ ’

 

‘ **you naked?** ’

 

‘ _Yup._ ’

 

‘ **totally naked?** ’

 

‘ _Yeah._ ’

 

‘ **show me.** ’

 

Cas’ stomach flips almost nervously at the thought. He’s never done that before, and he can only imagine what it would be like.

 

‘ **as long as you’re okay with it. don’t do anything you’re uncomfortable with,** ’ Dean says, always wanting to make sure that he’s never pushing Cas. He waits for a moment, sees the little typing bubble pop up then back down. Dean figures Cas might be writing out something or thinking over it a little more but then all of the sudden a picture pops up. A picture of Cas’ dick hard and aching laying on his toned and tanned tummy. Dean practically salivates at the picture as his brain pretty much short circuits. 

 

‘ _You touching yourself yet?_ ’ 

 

The message pops up right under Cas’ picture. Dean huffs a breath of laughter as his hand creeps down to his own aching cock.

 

‘ **well yeah now i am,** ’ Dean replies. Cas smiles, wrapping a hand around himself.

 

‘ _Good._ ’

 

‘ _Show me._ ’

 

Dean smirks at the message, and has absolutely no problem opening up the camera and taking a picture of him with his dick in his hand, then sending it to Cas. 

 

Cas holds back a moan at the picture. 

 

‘ _God, I wish I was there with you right now,_ ’ Cas types out, beginning to stroke himself leisurely. 

 

‘ _Wish I could be fucking you._ ’

 

‘ _Kissing you._ ’

 

‘ _Sucking you._ ’

 

Dean bites his lip and groans softly. He tightens his fist around his cock, moving it a little faster.

 

‘ **more,** ’ Dean replies simply, and Cas grins.

 

‘ _If i were there I’d get you on all fours, just like you said you liked. I’d finger you nice and slow and gentle just to make up for how hard i would fuck you. And i would stroke you the whole time, jack you off nice and slow, but then alternate between jacking you off so fast you’re about to come._ ’

 

‘ **cas,** ’ Dean replies, and Cas can tell that he’s getting desperate. 

 

‘ **please.** ’

 

‘ _Are you getting close?_ ’

 

‘ **yes.** ’

 

‘ _I want you to come Dean. I wish that i could be there but since i can’t I’ll just settle for you telling me how hard you came just from me telling you how I’d fuck you. Just imagine what i can do for you once I get to see you again._ ’

 

Dean reads over the message a few times, thinking it over as his fist moves even more furiously over his cock. Finally, finally he can feel himself tipping over the edge, and finally he’s coming, suppressing a groan as he throws his head back against his pillow, his hips bucking up into his hand, come spurting over his fist, over his stomach.

 

Dean rides out what he has to put down as a spectacular orgasm until he’s spent, a pleasant buzz running through him. He remembers Cas, and immediately grabs his phone with his free hand, the one that isn’t covered in come.

 

‘ **i just came,** ’ Dean types back lamely, then frowns a bit.

 

‘ **that sounded really bland, sorry.** ’

 

‘ **it was a fucking good orgasm though,** ’ Dean clarifies. 

 

‘ _Wanna help me out with mine then?_ ’ Castiel inquires, and Dean immediately feels a little bad that Cas hasn’t come and that Dean had forgotten about it. He tries to think of what he could say that would make Cas come, but then he gets an idea.

 

Cas, on the other hand, is still fisting his cock, biting his lip, waiting for something to push him over the edge. He knows it won’t take much, and he could probably bring himself to come himself, but he wants Dean to say something to get him there. And, sure enough, after what feels like an eternity, something pops up on his phone. A picture. A picture of Dean’s softening cock laying on his stomach in a pool of come. 

 

Cas immediately has to hold back a moan as he moves his hand even faster, blinking at the picture until he’s coming too, all over his stomach, all over his hand. He bites his lip hard through it, his hips twitching until finally he’s coming down from his high, letting out his breath, chest heaving. After a moment, he collects himself as best he can, fumbling for his phone.

 

‘ _fuck, dean,_ ’ he types out, hitting send, his cock twitching again at the prospect of seeing the picture once more.

 

‘ **did you come?** ’ Dean questions.

 

‘ _yeah,_ ’ Cas simply replies. Dean smiles on his end.

 

‘ **good.** ’

 

‘ **well, i’d say that that went pretty well for our first time sexting,** ’ Dean says, smiling softly.

 

‘ _Agreed actually,_ ’ Cas replies.

 

‘ **we’ll have to do it again, just so we can, y’know, get better at it.** ’

 

‘ _Yeah and I’m gonna have to fuck you right away when I get back because you’ve reminded me how much I miss you,_ ’ Cas types out. Dean smiles.

 

‘ **i’m definitely not opposed to that.** ’

 

‘ _good._ ’

 

‘ **well, hey, we’re both messes so why don’t you go take a shower or something and i’ll do the same. i’ll text you later to say goodnight, alright?** ’ Dean says.

 

‘ _sounds good to me,_ ’ Cas replies, still smiling.

 

‘ **good. i love you.** ’

 

‘ **thanks for making me come my brains out.** ’

 

‘ _i love you too dean. thank you for doing the same for me,_ ’ Cas teases back.

 

‘ **no problem, babe,** ’ Dean sends back, complete with the little kissing emoji. Cas locks his phone and tosses it aside, sighing contentedly. Dean is definitely a keeper.

**Author's Note:**

> Alright, you guys know the drill. Kudos, comments, feedback, everything is wonderful and please let me know what you thought!! I hope that LL OF YOU GUYS ARE DOING WELL oh shit whoops I hit caps lock. Yeah, hope you guys are good and thank you so much for reading!!!


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